Seeing Kyoto and Osaka makes for a nice long weekend. Kyoto, the old capital, is the gem of Japan. Sure, it's touristy, but for a reason: it's simply beautiful. You can easily get lost just wandering around the town, taking in all the sights and sounds.
Osaka is the second largest city in Japan, and is always in Tokyo's shadow, though the locals won't be too happy if they hear you say that. You can see Osaka in a day. Like Japan in general, it's a place to experience. Wander around the city at night and let your senses get battered.
Osaka is your typical huge Asian city. There isn't a lot to see; you can do it all in a day. Osaka-jo Castle is impressive, and the temples such as Shitenno-ji and Sumiyoshi Taisha Shrine are worth a look.
WHAT TO DO:
Kyoto: walk around the Gion district, full of geisha rooms and watering holes. It's marred by modern buildings, but still pleasant enough to stroll through. Oh, there are more temples here, too. Walking along the Kamo-gawa River in the evening is one of my best memories of being in Japan.
Osaka: Kita-ku is a lot of fun; you'll feel what modern Japan is all about. In Minami-ku, you have to check out the ridiculous America-Mura, or, "America Village!" This is teenie-bopper land. You'll be in awe of the fake Statue of Liberty and huge Tower Records Store.
WHAT NOT TO DO:
Don't walk into a restaurant or bar and order away, which is a general rule you should follow in Japan anyway, to prevent money from flying out of your wallet.
WHERE TO EAT:
I'm researching the name of this treat, but in Kyoto, look for restaurants where you cook what looks like a vegetable pancake in front of you! It's a cheap meal and very tasty! If you're on a budget, you can subsist on fare from convenience stores like Family Mart and Lawson's. You can get pretty good cheap sushi there. If you're adventureous, try those triangular-shaped rice goodies wrapped in seaweed. They aren't bad! Look out for black pepper flavored popcorn! Learn the hirigana for lunch, "ranchi". You can get pretty good lunch deals for about 500-600 yen.
There are plenty of places in Kita-ku if you're looking for grub in Osaka. The Food Park in the Umeda Chika Center has a lot of small restaurants. In Minami-ku, Dotomburi Street has countless eateries. Of course, you could always have the McD's specialty, the ham and egg hamburger.
WHERE TO STAY:
Cheap accomodation is tough to find in Kyoto. I highly, highly recommend the Tani House in northern Kyoto (075-492-5489). The owners are a darling older Japanese couple who make you feel welcome! It's a gorgeous old home where you'll feel like you're in old Japan. Take the 206 bus from Kyoto Station (terminal B4), and get off at Kenkun-jinjamae stop; it's near Daitoku-ji temple. If you can't find it, ask someone; people in this neighborhood were really nice.
You're better off staying in Kyoto and then spending a day in Osaka on your way home. Try the Osaka-fu Hattori Ryokuchi Youth Hostel, between Kita-ku and Minami-ku (06-862-0600).
WHAT TO SEE:
In Kyoto, everything. This page isn't big enough to write everything. Decide if you're into palaces or temples, and decide from there. In central Kyoto: the Imperial Palace, Nijo-jo Castle, Nijo-jinya. Near Kyoto Station: Nishi Hongshan-ji Temple, Higashi Hongan-ji Temple, To-ji Temple. Can you see there are a few temples here? Eastern Kyoto is incredible. Definitely spend a lot of time here. Don't miss Sanjusangen-do Temple (awesome!), Kiyomizu-dera Temple, the Sannen-zaka and Ninnen-zaka Walk, and the Kodai-ji Temple. Western and northwestern Kyoto is lovely as well. You're in the DC of Japan: you could spend a week here easily!